2-(4-bromophenyl)-N,N-dimethylethanamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of LiAlH4in ether (5 mL) was added a solution of 2-(4-bromophenyl)-N,N-dimethylacetamide (1.1 g, 4.5 mmol) in 5:1 ether/THF (12 mL), giving a small exotherm. The mixture was stirred at room temperature for 3 h, refluxed overnight then cooled to 0° C. Water (0.5 mL) was added dropwise and the mixture stirred vigourously for 3 h, then poured into 1 M NaOH and extracted with ether. The organic phase was washed with brine and dried over MgSO4. Purification by flash chromatography (4% to 8% MeOH/dichloromethane+0.5% ammonium hydroxide) provided 132 mg of 2-(4-bromophenyl)-N,N-dimethylethanamine. giving a small exotherm refluxed overnight then cooled to 0° C the mixture stirred vigourously for 3 h extracted with ether The organic phase was washed with brine dried over MgSO4 Purification by flash chromatography (4% to 8% MeOH/dichloromethane+0.5% ammonium hydroxide)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(4-Bromophenyl)-N,N-dimethylethylamine (6.8 g) was refluxed under heating with magnesium for 1 hr to prepare a Grignard reagent, which was reacted with DMF to give the objective 4-(2-dimethylaminoethyl)benzaldehyde as an oil (4.2 g).